What excellent question have you asked or been asked lately? How did it affect your relationship with the person asked/asking?

Ever since I started working with my life coach in 2005, I have practiced asking more and better questions in any encounter, in all life domains. The returns on this investment of presence and curiosity–idea generation, heightened conversation, and deepening connection, among others–far outweigh the costs of occasional awkward pauses and uncomfortable deflection.

I wonder, however, if I give enough time or energy to answering the interesting quesitons I ask?

Why, for instance, do I behave so differently with people in and out of my family? I feel like the same person in both contexts, and everybody knows the same me; yet I know I show up not the same at home as outside. Fascinating.

Today was Day 190 of my morning pages practice. Looking back, much of the journaling consists of lists, plans, recollections, and reflections. The same questions arise recurrently, mostly centered around behavior and relationships, and I attempt to answer overtly about half the time. Also fascinating! I feel comfortable with this state of things, as the simple act of writing them down and letting them sit on and below my consciousness day to day allows me to consider them slowly. Persistent questions point me to my core values, purpose, and goals. I feel no rush to formally answer these existential, identity-related, philosophical inquiries. I tell the story that simply marking their re/o-ccurrence pins them to some level of awareness where I can return regularly, like periodically adding brushstrokes to paintings that live in various rooms of my mind, heart, and life, when I happen to walk by. These rooms are bright and airy, each equipped with a sturdy easel, thick canvas, rich color palette, and full set of implements to create and revise, ad lib. I feel calm and focused, reassured that whatever is happening on any given day, I have time and energy set aside to process and digest, coming to clarity organically and as needed, all in good time. My morning pages facilitate insights and understanding regularly, and I see this practice sticking for the foreseeable future.

What I really relish, however, is engaging in questions, exploration, and discussion with other people! I wonder if this is how I make friends, actually? It does not matter if I just met you or I’ve known you my whole life; if you’re willing to dive with me like humanities nerds in a submersible to plumb the depths of open and honest questions and wild ideas of possibility–about anything from language to muscle physiology, human nature to politics, phylogeny to music–I might soon profess my undying love for you and chase you for more of that energizing connection. It is most often with friends, in those small, relaxed, meandering, sometimes calorie-laden gatherings, where nascent and novel answers to delightful questions so beautifully emerge and bloom. I carry my journal everywhere, to capture these pearls when they drop, as though gifts from the gods of sentience and relationship.

People crave deeper connection desperately now, in our increasingly chaotic, impersonal, and globalized world. I see references to the 2015 New York Times article “36 Questions That Lead to Love” regularly (that’s probably the algorithm, right?). If you cannot access it, see the original research article by Arthur Aron et al, “The Experimental Generation of Interpersonal Closeness: A Procedure and Some Preliminary Findings” with the questions listed at the end. Organized into three sets of increasing intimacy, the exercise invites us to ask our conversation partners questions such as, “What would constitute a perfect day for you?” “What is your most treasured memory?” and, “Complete this sentence: ‘I wish I had someone with whom I could share …'” From NYT: “The idea is that mutual vulnerability fosters closeness. To quote the study’s authors, ‘One key pattern associated with the development of a close relationship among peers is sustained, escalating, reciprocal, personal self-disclosure.’ Allowing oneself to be vulnerable with another person can be exceedingly difficult, so this exercise forces the issue.” I have the article bookmarked on my phone, and have yet to invite anyone to answer with me–maybe I’ll set an intention to do so on my upcoming friend dates? Part of me thinks I’m doing fine connecting on my own, and you never know, this could be truly next level.

Renowned psychologist Esther Perel created a similar game in 2021, Where Should We Begin, now in its 2nd edition. This query is how she historically initiates therapy sessions with clients. Questions in the game include, “I can’t believe I got away with…” “My latest crush is…” and, “My favorite love story to tell…” The box includes questions that range from lighthearted to serious, to sexual and beyond, which positively tickles me–because it’s all just life. In this age of polarization and easy mutual disdain and disconnection, games like this can help us all recognize our shared humanity.

I have purchased yet a different box of questions for connection, How Deep Will You Go? Its creators describe it as “a game of deep conversation without worrying what to ask, to feel closer in a way you never felt before.” Three levels of questions are labeled Ice Breakers (“What motivates you in life?”), Confessions (“Why have you kept going?”), and Getting Deep (“What is something you don’t tell most people?”). Reading the cards, I imagine with whom I’d want to delve. It depends on the question(s), of course, and also context and mood. I can picture a small friend group setting for the playful ones, and core belief/value ones as actual ice breakers for purposeful group work, such as a Braver Angels workshop. For the more intimate questions, though, I picture a one on one meeting, with plenty of preface and mutual agreement to actively engage in deepening personal connection.

Of course, interpersonal closeness is an iterative process: Other than the most superficial queries, the willingness to ‘go deeper’ requires some level of established trust and safety. That can take a while, depending on a multitude of factors. But once that foundational rapport is achieved, subsequent connection facilitated by these questions, one by one, may unfurl like the slow and steady inflation of a hot air balloon from the ground, lifting us gently together to affinity and affection we could never achieve where we started.

Connection decks like Where Should We Begin and How Deep Will You Go? make me so optimistic. I have loved and tried to ask questions like this for years, and now I feel validated. What if we all opened up to one another just a little bit more, just a little more often? What if we held one another’s hopes, joys, struggles, regrets, dreams, and confidences with a little more respect and reverence? What if we approached one another, friends and strangers alike, with the assumption of caring and mutual well wishes, looking to hold one another up, rather than with suspicion and wariness? And what if we rewarded such unearned generosity of spirit with reciprocal kindness?

The practice of mindfully asking deeper, more personal, loving, and intimate questions could go a long way to bridging our seemingly insurmountable differences; we all need this right now. It’s not appropriate in every encounter, of course. We must attune to context and opportunity, and act (ask) with confidence and humility. And that’s also the point, isn’t it?

The more present we are to one another’s vibrations, our moods and energies, the more likely we are to connect in earnest, regardless of what questions we choose to ask or not.

Understanding, validation, belonging, closeness, intimacy–we humans thrive when we feel these often and deeply. I still have hope that we can do it better.